Water → HCID 11583486, compound

HRID 1958896Notes

Reaction equation

HRID 1958896 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:25][CH2:26][C@@H:27]2[CH2:31][O:30]C(C)(C)[O:28]2)[N:12]=1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:25][CH2:26][C@@H:27]([OH:28])[CH2:31][OH:30])[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53628342HCID 53628342, compound

Product 1

HCID 11583486HCID 11583486, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-4-pyrimidinyl]-1-azetidinesulfonamide (the product of step (0.48 g) in methanol (5 mL)/H2O (0.1 mL) was added pyridinium p-toluenesulfonate (0.12 g) and the mixture was stirred at reflux for 2 h. The reaction mixture was evaporated, suspended in H2O and extracted with EtOAc (×2). The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was triturated with DCM to give the title compound as a white solid. Yield: 0.30 g

Workup

  1. temperatureat reflux for 2 h
  2. customThe reaction mixture was evaporated
  3. extractionextracted with EtOAc (×2)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with DCM

Sources & evidence

ORD record
ord-e8f66392068945a1b3ec3ab4848548d0
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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